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Book your trip with confidence — We only work with the best local guides that know where to put you on fish.

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You're in good hands

Book your trip with confidence — We only work with the best local guides that know where to put you on fish.

About Your Trip

Water Type

Deep Sea

Skill Levels

Beginner, Intermediate, Advanced

Weather

You won’t lose your deposit if the trip is canceled due to weather.

About Your Trip

We offer half day, 3/4 day and full day trips. It takes us 20 mintues to reach fishing grounds. Just a few mintues from shore and we're in 1000ft+ and that is what makes deep sea fishing great in the Cayman Islands.

We provide a knowledgable Captain and First mate. We won the Anglers award for 2024 and 2025, so you're in good hands.

We also provide, cooler with ice, water, soda, gear and bait. No fishing license is required once you book with us.

We pick up from the closest dock to you if that's convenient.

We use a few techniques which never fails - trolling, drifting/chucking, jigging and live baiting.

Amenities

Water Type

Deep Sea

Skill Levels

Beginner, Intermediate, Advanced

Tackle

All rods, reels, and tackle are included.

Fish Cleaning

This guide will clean your catch for you.

Beer

Feel free to enjoy responsibly, but please no glass.

Music

You can play your own bluetooth music.

Boat Restroom

This boat has a restroom.

Location

This guide can be flexible with the departure location.

Weather

You won’t lose your deposit if the trip is canceled due to weather.

Kid Friendly

This trip can cater to small children.

Flexible Cancelation

This trip can be canceled up to 3 days before the trip.

Physicality

This trip requires an average level of physical activity.

Live Bait

Live bait is not used on this trip.

Disability Friendly

This trip is not suited for those with disabilities.

Lunch

Please provide your own food / snacks.

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Pricing Matrix

	4 hours	6 hours	8 hours
1 Person	$1,300.00	$1,700.00	$2,200.00
2 People	$1,300.00	$1,700.00	$2,200.00
3 People	$1,300.00	$1,700.00	$2,200.00
4 People	$1,300.00	$1,700.00	$2,200.00
5 People	$1,300.00	$1,700.00	$2,200.00
6 People	$1,300.00	$1,700.00	$2,200.00
7 People (two boats)	$2,600.00	$3,400.00	$4,400.00
8 People (two boats)	$2,600.00	$3,400.00	$4,400.00
9 People (two boats)	$2,600.00	$3,400.00	$4,400.00
10 People (two boats)	$2,600.00	$3,400.00	$4,400.00
11 People (two boats)	$2,600.00	$3,400.00	$4,400.00
12 People (two boats)	$2,600.00	$3,400.00	$4,400.00

Pay 15% of the price as a deposit today, with the balance due on the day of the trip.

About Your Guide

Dillan

Independent Guide

About Your Guide

Dillan

Independent Guide

Dillan and his team were born and raised on the shores of Grand Cayman, with saltwater in their veins and a lifelong connection to the sea. What started as a passion for exploration and time on the water grew into a commitment to sharing the island’s beauty with others.

As seasoned watermen and ocean enthusiasts, they specialize in creating unforgettable days on Cayman’s crystal-clear waters. Whether you’re snorkeling vibrant reefs, cruising the coastline, or simply soaking in the Caribbean sun, Dillan and his crew focus on delivering a seamless, welcoming, and detail-driven experience.

Professional, personable, and deeply rooted in local knowledge, this is a team that takes pride in turning time on the water into lasting memories. When you step aboard, you’re not just booking a trip — you’re exploring Grand Cayman with locals who truly love where they live.

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Start Location & Lodging Options

Your guide can be flexible with your start location.

You can work with your guide after booking to set a more specific start location in the area.

George Town, George Town, Cayman Islands

Areas Fished

Grand Cayman

About Your Boat

Boat Type: Center Console
Boat Manufacturer: Pursuit
Year Built: 2022
Boat Length: 27'

About Your Boat

Boat Type: Center Console
Boat Manufacturer: Pursuit
Year Built: 2022
Boat Length: 27'
Boat Restroom: Yes
Engine Manufacturer: Mercury
Total Horsepower: 399
Number of Engines: 1
Additional Amenities: livewell, fresh water wash down, toilet, Bluetooth stereo, vhf radio, snorkel gear, life vest, life ring and sink.

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Trip Details & Amenities

Water Type

Deep Sea

Skill Levels

Beginner, Intermediate, Advanced

Tackle

All rods, reels, and tackle are included.

Fish Cleaning

This guide will clean your catch for you.

Beer

Feel free to enjoy responsibly, but please no glass.

Music

You can play your own bluetooth music.

Boat Restroom

This boat has a restroom.

Location

This guide can be flexible with the departure location.

Weather

You won't lose your deposit if the trip is canceled due to weather.

Kid Friendly

This trip can cater to small children.

Flexible Cancelation

This trip can be canceled up to 3 days before the trip.

Physicality

This trip requires an average level of physical activity.

Live Bait

Live bait is not used on this trip.

Disability Friendly

This trip is not suited for those with disabilities.

Lunch

Please provide your own food / snacks.

Target Species

Color-coded seasonality below is based on .

View Full Species Seasonality Chart »

Get it while it's HOT!
This species is in play.
You might get lucky (as long as things are in-season).
Couldn't tell ya! (no data)

Techniques

Artificial Lure Fishing
Cut Bait Fishing
Drift Fishing
Heavy Tackle Fishing
Jigging
Live Bait Fishing
Sight Casting
Trolling

Everything Else to Know

Everything is included, but we also recommend bringing sunglasses, sunscreen, weather-appropriate clothing, and anything else you might want on the trip.

You'll need to buy a fishing license before getting out there. Find out more about licenses here.

We use a cashless autopay system. We'll send you a boarding pass, and on the day of the trip, your guide will scan your boarding pass to automatically transfer the remaining balance. The only cash needed is to tip your guide (we recommend 20%).

Cancel for free up to 3 days before the trip and receive credit back to your account. Cancelling within 3 of the trip will forfeit your deposit to the guide. Day-of cancellations and no-shows will be charged the full balance of the trip to their card.

In the event of inclement weather you'll be covered by out 100% Weather Guarantee and will not lose your deposit.

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First Time Booking with Us?

Captain Experiences is home to thousands of quality, vetted fishing, hunting, and other outdoor sports guides across the US and beyond. Our mission is to Unlock the Outdoors by making it quick and easy to book the trip of a lifetime every time with our Damn Good Guides.

We vet our guides and only partner with the best of the best. Our guides do their very best to keep you safe, show you a great time, and send you home with a memorable experience shared with family and friends.

Once you've paid your deposit at checkout, we'll send you a QR Code boarding pass. Just show your guide your boarding pass on the day of the trip, they'll scan it, the remaining balance will transfer automatically, and you'll be all set to get out there. Just make sure you bring a cash tip for the guide!

In the event of inclement weather, our guides will check the conditions and make the final call on whether its safe to go on the trip. If they decide the trip needs to be postponed, we'll work closely with you to reschedule or provide a credit for the full deposit, which can be applied to any of our trips in the US and beyond.

Each trip's price is determined by the guide and reflects all associated costs. A significant factor in pricing is often the type of boat and the corresponding fuel expenses. Additional costs may include leases, marina or slip fees, and the expenses involved in providing and maintaining the necessary gear for your trip.

After booking your trip, we'll connect you directly with your guide to discuss additional details. In the meantime, our team is here to answer any questions via email, text, or phone.